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Hello Marianne,
make sure that the attachments (if any) are not too large since some email services do not allow those.
In some cases, an email containing potentially offensive vocabulary can be rejected automatically.
Make sure that your recipient looked in his junk email folder and also that he did not block messages coming from Yahoo.
If those steps do not solve your issue, please tell me which email service is your recipient using.
Regards,

Sometimes various ISPs (Internet Service Providers) block port 25, which is the default port used by email providers like Yahoo configured on outlook. There is an easy way to fix this, and I will provide some pictures to illustrate it. There might be some slight differences depending on the version of outlook and/or outlook express you are using, if so let me know and I will clarify as I can.

From the "Tools" menu select "Accounts."

Select your Yahoo! POP account and click "Properties".

Click the "Advanced" tab. Under "Outgoing mail server (SMTP)," check the box next to "This server requires a secure connection (SSL)." (This step is not required if you choose to use port 587).

Enter port number 465 (recommended) or 587 in the "Outgoing mail (SMTP)" field.

Are you using Yahoo or other 3rd party email or a client (like Outlook)? If you're using Outlook (or other client) you need to re-setup your email address and password so Outlook can connect with your email source.

Outlook Express is just a software which can send and recieve emails from any email account configured on it(Outlook Express). regardless of yahoo, gmail, comcast.net ,aol.com etc.

So if you want to change your email address and want to use it on outlook express, you need to first create an email account by going to the website on which you want to create an email address.

Once you have created the email address we can look for the POP/SMTP server settings of that particular email account on the internet .
Once we have those(POP/SMTP) addresses we can configure Outlook Express to send and recieve emails for your new email account.